How do you judge which contractor to hire for repairs?

WE have to have some repair work done on our roof and are hiring a contractor to do it. I know all the stuff like checking their insurance and business license. But how do you judge who is the most likely to do a good job?
-The guy who gave the highest bid, but was honest about it being expensive and really seemed to have his sh*t together?
-The owner/estimator who gave a good estimate and seemed to know what he was talking about, but came to the estimate rather unprepared?
-or the middle bid who was prepared and knowledgeable but is from a larger company and will not be the one actually doing the work or heading the crew?
Any thoughts or related stories?

I certainly would use the Internet for all of my fact-checking when it comes to contractors...
Having been a property manager, I've seen the many sides of the contracting business and some of those sides aren't too pretty!
Todays Internet power can help you find good people but you still must be able to judge their characters in person...
Be sure that the contractor has come to you through a reputable referral system and that he can produce references and the necessary licenses for the project(s) that you want completed...
Also, nowadays, a criminal background check might be a necessity, sorry to say...
Also, you should choose the time of the year when you want the job done very carefully...
There are many stories of low-life contractors victimising homeowners who chose to have new windows, for example, installed in the winter and the contractor removed all of the old windows and then refused to install the new ones until he got more money! He actually used the weather as an extortion tool!
I wish you the very best of luck with your project! :)
Please stay "on your toes" and ask all the right questions. If you don't know the right questions, do a search for "Proper Questions To Ask Any Home Contractor" on
The link below:
http://www.usa.gov/Citizen/Topics/Family/Homeowners.shtml
I hope that this will help you stay ahead of the game! :)

i think you need to do alot of research on previous clients. that is the only way or check out the better business bureau or one of those companies. we had our roof done buy a friends friend who has a construction company and it has been the worst nightmare ever. we have an old house and just decided to do the roof to improve it. it now leaks. i have had so much damage to the inside it is not funny. we even called the guy and he never showed up.
just be wary. good luck.

I would see if you have a better business bureau near you, they rate companies and would know if any complaints against the company and any good feedback. Dont feel shy in asking them, if they are licensed and insured, as this is your home,etc to be repaired, and you deserve the very best.
Also, I do observe who seems to know the most and is organized. Many will provide references too for you upon request. Hope this helps you!